Adriamycin, an antibiotic compound which is usefull in the treatment of certain tumors is described and claimed in U.S. Pat. No. 3,590,028, to Arcamone, et al. A further procedure for the preparation of adriamycin will be found in U.S. Pat. No. 3,803,124 to Arcamone, et al. Said patent also discloses that the adriamycin may be prepared from daunomycine or its aglycone daunomycinone which are described and claimed in U.S. application Ser. No. 404,550, filed Oct. 6, 1964, by D. I. Marco, et al.
A total synthesis of daunomycinone has been disclosed by Wong, et al, (Canad. J. Chem., 51, 446 (1973)). This synthesis, while apparently operative, gives such small yields that its use as a commercially viable alternative to the fermentation derivation of daunomycin and adriamycin is not considered feasible.
A further approach to the synthesis of (+)-9-deoxydaunomycinone, another intermediate in the synthesis of daunomycin, is disclosed by the Applicant herein and coworkers in J. Amer. Chem. Soc., 97, 4425 (1975). This approach is quite different from the approach to the synthesis of daunomycinone to be described and claimed herein.
It should also be noted that the coupling of daunomycinone with the appropriate sugar to yield daunomycin (also known as daunorubicin) is found in Acton, et al., J. Med. Chem., 17, 659, (1974). The sugar, daunosamine utilized in the Acton synthesis of daunomycinone is disclosed in Marsh, et al, Chem. Commun., 973, (1967).